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Issue 9, 2015
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Tandem catalytic oxidative deacetylation of acetoacetic esters and heteroaromatic cyclizations

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Abstract

One pot syntheses of furan, thiophene, and pyrrole were accomplished by oxidative deacetylation using Mn(III)/Co(II) catalysts and the Paal–Knorr reaction from 1,5-dicarbonyl compounds, which are prepared from the conjugate addition of ethyl acetoacetate to α,β-unsaturated carbonyl compounds. The oxidative deacetylation and reductive cyclization of β-ketoesters derived from ethyl acetoacetate and o-nitrobenzyl bromides efficiently produced diversely substituted indoles.

Graphical abstract: Tandem catalytic oxidative deacetylation of acetoacetic esters and heteroaromatic cyclizations

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Article information


Submitted
20 Nov 2014
Accepted
22 Dec 2014
First published
22 Dec 2014

Org. Biomol. Chem., 2015,13, 2588-2599
Article type
Paper

Tandem catalytic oxidative deacetylation of acetoacetic esters and heteroaromatic cyclizations

Y. Ju, D. Miao, R. Yu and S. Koo, Org. Biomol. Chem., 2015, 13, 2588
DOI: 10.1039/C4OB02441A

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